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#1 Castle Rental in Caribbean w/ 125!~ALL 5 Star Reviews!!! Come & Just RELAX!!!

Bedrooms 4
Half Baths1
Space 669 m²
Property type castle
Minimum Stay 5 - 8 nights


About the property

Our CASTLE NOW has 125 ALL 5 STAR Guest Reviews Rent 1-4 MASTERS ALONE EASY!

Dear True Paradise Researcher,

We are very pleased to have your most kind interest in our version of True Paradise! The amazing Grand Outlook Castle on the beautiful and safe island of Anguilla.

Grand Outlook Castle IS the #1 Rental Option, out of 27,000+ other alternatives, in the entire Caribbean with 119 ALL 5-STAR ACTUAL guest reviews. Our testimonials are penned by THE ACTUAL folks who have paid for and enjoyed the full Anguilla/Grand Outlook Castle experience . ALL agree "WE will return!"

Guests from Thanksgiving wrote that their retreat to Anguilla and Grand Outlook Castle was both "Exquisite & ""Priceless". Two of our most recent families wrote " BEST VACATION EVER! " That is our mission for you also. Please read a few of our 116-5 star guest reviews.

Our ACTUAL prior guests' words tell the story you need to know to make the best decision for your retreat to True Paradise and your worthy efforts you have made to have found The Grand Outlook Castle.

Grand Outlook Castle IS located on a truly amazing site and our infinity edge pool faces each amazing sunset as does each separate bed chambers. ALL 4 bedroom suites are Master Bedrooms with private verandas and private 2 person hammocks... No drawing straws for that tricky 4th "bedroom" that was really a closet and no one wants. EVERY ONE in your group will have a best of house master suite. It's just a matter of the specific stunning views ALL our guests receive right from their bed!

Grand Outlook Castle WILL exceed you and your party's expectations. No image or description can ever replicate the experience of entering the castle's gated & flowered compound of bold oleander & bougainvillea with hummingbirds and distracting turquoise sea views. You will be drawn into the stunning castle designed specifically to expose you gradually to ever expanding sea views.

With each step, you move closer to a massive view of 'Mother Nature's' finest works. Guests are thoroughly captivated by the experience... your expectations will have already been exceeded!

Grand Outlook Castle IS EASY! Our rates include ALL fees & tax

Grand Outlook Castle is a truly amazing structure, on an amazing site and one of the best if not the best islands in all the Caribbean.

As we say most sincerely, 'Come… & Just Exhale! ” tm

Please read a few of our 79 oops 97 oops 100-ALL 5 STAR guest reviews; you too will absolutely agree! AND... 100% of ALL prior Grand Outlook Castle's guests happily confirm 'they WANT to return'. You will also!

Grand Outlook Castle is an AWARD WINNING, modern and stunning oceanfront estate. Grand Outlook Castle is a truly compelling venue for 2 to10 guests. Whether a family-friend reunion, anniversary-birthday celebration OR an intimate honeymoon for just 2, Grand Outlook Castle accomodates you ALL in grand fashion.

Our rates include all taxes/fees, are adjusted to accommodate your vision of spectacular Anguilla and the total number of guests within a very reasonable budget for true Paradise. Our castle's 1-4 bed chambers are ALL spacious MASTERS w/ BIG ensuite baths, A/C, very private balconies and amazing views.

Two bed chambers have stunning double headed outdoor showers and ALL are most accommodating to even the most discriminating of guests. Everyone in your group receives a most wonderful private space with complete privacy and stunning views from every window with large sliding glass doors onto private terraces.

Rent one, two, three OR all four bedrooms and regardless of that number, the entire castle and staff is your's alone during your stay. No rooms are locked out to you. Grand Outlook Castle will truly be your private castle and your most memorable vacation home!

After being open just six seasons, our same guests have returned for 3, 4 & even 5 consecutive visits AND some have already booked again for 2017... so if you are interested in our very unique Anguilla experience, feel totally at ease in contacting us right away. We are licensed to offer Travel Guard trip insurance so you can be totally comfortable booking the castle well in advance.

Once you arrive at Grand Outlook Castle, you will find it hard to leave! Children and adults have been know to shed a tear when having to leave for home.

One of the many reasons Grand Outlook Castle won these special awards is that it simply has truly amazing sea views both day & nite. A very PRIVATE & very SECLUDED infinity pool w/ the BEST sunset views on Anguilla! 2 OUTDOOR showers. Pool deck cooking on GE Monogram gas grille, 2 unit stove & dolphin sink. LARGE Plazma TV in entertainment area,TV's in 3 bedrooms, iPod hook-up, pool deck tunes, video library and FAST! Wi-Fi throughout.


Performance granite kitchen w/ GE Monogram appliances & 5 seat bar for perfect entertaining. Hiking access to Crocus, Limestone and Famous Little Bay Beaches. Grand Outlook Castle has 99 ALL 5 STAR Guest Reviews MOST of any villa on Anguilla. Take 5 minutes & read a few. They will educate & entertain you & then ask us ANY ?'s.


The castle's views South include St Barts & St. Kitts which are 27 & 64 miles away. Grand Outlook Castle's views are amazing in virtually any direction. ALSO, you will receive the personal concierge services of Elise & Paul Grand Outlook Castle's 'Envisioners', builders and owners. They will insure your transition to Paradise is flawless. Most importantly, even if your first visit to Anguilla, you can easily and FINALLY... Come & Just EXHALE! sm This will be a simple and very relaxing VACATION!

Your BEST airfare prices? Fly into St. Martin (SXM). JetBlue flies direct from JFK, BOS & San Juan (SJU). USAirways from Charlotte (CLT) & Philadephia (PHL). American direct from Miami (MIA) and Delta direct from Atlanta (ALT)


Good local food shopping and the ability to bring frozen meat onto Anguilla from home for your personal use save hundreds of dollars... We will show you how.

1.) * Rental rates include all island fees & taxes, NO ADD-ONS and NO departure surprises!

2.) * Rental rates adjusted to the size of your group. From 2-10 guests. Regardless of you size group, you will have the castle soley for your group or family.

Safe, private & comfortably secluded. True relaxation in Paradise! OH, those views? They are 'AMAZING!'.

* Rental rates are very reasonable with the group size & seasonal adjustments.

* Staff is at your direction. Want to sleep in a couple mornings? Just let Ms. Rolyn know and she'll come by whenever you desire.

Our staff loves YOU!

You will love our staff too.

* All Grand Outlook Castle's extraordinary concierge services provided for you are at our 'COST'. Do we book vehicles for you? YES! Our best cost is your cost. Desire a pool deck massages? Do it! Our best cost is your cost.

We not only have some of the very best villa rental rates but many other ways to save you money on food, services & shopping. (Some are personal 'secrets' so you must speak with us to learn them ALL) We do like to share them with any potential guest. We make our version of True Paradise very budget friendly for you. When you and your family or group rent GOC, your nightly room cost ranges between $249 to $499 including all taxes and all fees which makes these rates the BEST!

* Washer & Dryer at the castle for your use... you do NOT need to over pack.

* Your chosen vehicles are delivered to the castle for your arrival EASY!

* Full pre-departure Anguilla information package sent to your home including a hand notated island map, recommendations and EASY castle instructions.

ALL your questions answered before you leave for Anguilla and Grand Outlook Castle. We want to answer every one of your questions so you can enjoy and explore Paradise on your own immediately UPON your arrival.

* Never rented a castle over the Internet before? *A little uneasy with the whole idea? Understandable! CALL US! *Your total peace of mind is what our goal is during you entire Grand Outlook Castle experience.

The Travel Channel ranked Anguilla NUMBER ONE in the WORLD! w/ best all around beaches

Conde Nast Traveler wrote in 2012, 'Many Caribbean islands would be grateful for just one of Anguilla’s estimated 33 powder white beaches'

Visit our Facebook page! Search 'Grand Outlook Castle-Anguilla' @ Facebook and learn more about why Grand Outlook Castle is so unique, fun and desirable

Book With Confidence!! We are licensed to offer Travel Guard Insurance since 2007. A villa MUST be trustworthy to have such an approval!

HERE'S what was written by an 'expert' on Anguilla and guest to Grand Outlook Castle!

... 'Anguilla is a sleepy little island named after an eel due to its shape. Twenty years ago, it began to open its eyes and realized it had no industry to promote and less to do. Locals could barely grow any crops. They had beaches and blue water, but they always had that and took it for granted. Not until outside interests were searching for virgin beaches, did Anguillans discover what was right under their noses: unrivaled beaches and ocean that surpassed any in the world. Resorts soon began to invade the shoreline: Cap Juluca, Cuisinart, Malliouhana, all five star resorts. Meanwhile, the rest of the Caribbean was building on every square inch of land with no limitations and became very commercialized.

Fortunately, Anguilla has remained a sleepy island, but now the locals have jobs, employed by the resorts and their friendly demeanor reflects their gratitude for tourism. It is the ideal place for a quiet retreat, tranquil, serene, and private. Although the general dictum for an island hotelier is 'don't leave the beach', Elise & Paul followed their hearts and built the newest villa on the top of a mountain in the form of a castle. Although the island is only 16 miles long and 3 miles wide, GRAND OUTLOOK CASTLE is a secret.

As always, if any questions arise, please feel at ease in contacting us.


Elise & Paul Alegr

More Details

Elise & Paul
Member since: 2004
Speaks english, french, german, spanish, portuguese, italian, English, Greek, Spanish, Italian, Portuguese & AMC
Response time
Within a day
Response rate
Calendar last updated:
21 April, 2017

About Elise & Paul

In February 2003, Elise and Paul found 'Anguilla' on their very FIRST visit and knew immediately Anguilla was a very special island.


Elise & Paul had been 'touring' the Caribbean for the 20 years' prior looking for their special Paradise. Anguilla was that True Paradise.

Anugilla has the very best beaches, warmest people and numerous wonderful restaurants in all price ranges.


Elise & Paul found the castle's site on that very first visit and actually put a deposit on the land while drinking a 'Jim & tonic' at Roy's restaurant when it was down in Crocus Bay.

Elise and Paul would not have built Grand Outlook Castle anywhere else on Anguilla... Elise has sincerely noted... 'It is the grandest site we could find on Anguilla.'

We bought the site in 2003 and started building Grand Outlook Castle in 2004. The Castle was completed late in 2007. OVER three years of very excellent planning and very hard labor but well worth the outcome.

We have now have had over 2,500 guests in just 7 seasons and have received 87! all 5 star reviews; THANK YOU! We love it when guests say they find it very hard to leave what we were blessed in having created for your enjoyment... & ours too! Grand Outlook Castle Anguilla!

As we say & sincerely mean @ Grand Outlook Castle 'COME... & Just EXHALE!' tm

Elise & Paul purchased this castle in 2003

Why Elise & Paul chose Caribbean

Best views on Anguilla period! Serene & secluded. Plenty of room and privacy for 2-8 adults or possibly 10 with younger children. Private and safe with an actual castle tower with nearly 300* views. If unlimited views soothe you, Grand Outlook Castle is one of your best choices. Large ensuite bedrooms are spacious and comfortable. TWO with double headed OUTDOOR shower. Save time and have double the fun by showering in tandem. Large pool deck with simply massive views. A sense of being somewhere special, unique and relaxing. ALSO, as of 3/17/2015, Grand Outlook Castle Anguilla has 4,555 'likes' on Facebook. When you visit, you will really 'Like' GOC ALSO!

GOC always exceeds our guests expectations. Why? Because with all the pictures and all the 5 STAR reviews one MUST be at Grand Outlook Castle to understand and 'feel' the actual experience. as we say and sincerely mean... 'COME... & Just EXHALE!' tm

What makes this castle unique

Grand Outlook Castle is so very comfortable with both large communal spaces, quiet alone places and amazing views that make it simply hard to leave. Grand Outlook Castle is located in the middle of Anguilla so getting to any beach, all major shopping and any restaurant quite easy. We are on the second highest point on Anguilla so you can see both the Atlantic Ocean and Caribbean Sea at the same time. You can see St. Barths which is 24 miles to the southeast AND on a really clear day, you can see St. Kitts which is almost 60 miles away. Being 180 feet above the sea gives viewing a truly panoramic quality. Grand Outlook Castle is a photographer's dream come true. Come and bring your camera.

Anguilla is a sleepy little island named after an eel due to its shape. Twenty years ago, it began to open its eyes and realized it had no industry to promote and less to do. Locals could barely grow any crops. They had beaches and blue water, but they always had that and took it for granted. Not until outside interests were searching for virgin beaches, did Anguillans discover what was right under their noses: unrivaled beaches and ocean that surpassed any in the world. Resorts soon began to invade the shoreline: Cap Juluca, Cuisinart, Malliouhana, all five star resorts. Meanwhile, the rest of the Caribbean was building on every square inch of land with no limitations and became very commercialized. Fortunately, Anguilla has remained a sleepy island, but now the locals have jobs, employed by the resorts and their friendly demeanor reflects their gratitude for tourism. It is the ideal place for a quiet retreat, tranquil, serene, and private.Although the general dictum for an island hotelier is 'don't leave the beach', Paul Alegria followed his heart and built the newest villa on the top of a mountain in the form of a castle. Although the island is only 16 miles long and 3 miles wide, GRAND OUTLOOK CASTLE is a secret. Ask anyone on the island where it is and nearly all will

Guestbook comments from the owner

We, at Grand Outlook Castle, just received this e-mail from Judy who stayed at the castle during November 2013. Her words speak for themselves. THANKS Judy!

Hi Paul,

Just wanted to drop you a quick note. Just returned from Mexico, even though

it is so easy to get there and there is no cooking, we all agreed our time at GOC was absolutely our favorite vacation ever!

Nov 2013
  • 1 of 8


Accommodation and facilities for this holiday castle rental in Anguilla

Property Type:
  • castle
  • Guests provide their own meals
  • Housekeeper Included
Floor Area:
  • 669 m²
House Rules:
  • Max. occupancy: 10
  • non smoking only ...
  • pets not allowed
  • Events Allowed
  • children welcome ...
Location Type:
  • Beach ...
  • Beach View ...
  • Beachfront ...
  • City Centre ...
  • Near The Ocean ...
  • Ocean View ...
  • Oceanfront ...
  • Rural ...
  • Water View ...
  • Waterfront ...
  • Waterfront ...
  • Adventure
  • Away From It All
  • Budget
  • Family
  • Historic
  • Romantic
  • Spa
  • Sports & Activities
  • Tourist Attractions
  • Activities Guide
  • Air Conditioning ...
  • Alarm Clock
  • Broadband Access ...
  • Ceiling Fans
  • Clothes Dryer ...
  • Filtered Water
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room
  • Local Activities Guide
  • Local Maps
  • local restaurant guide
  • mobile phone ...
  • Parking
  • Parking Off Street ...
  • Safe
  • Security System
  • Telephone ...
  • thermos flask
  • Toilet Paper
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet ...
  • 4 Ring Stove
  • Blender
  • Catering Available ...
  • Coffee Grinder
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils
  • Dishwasher ...
  • Freezer ...
  • Grill
  • Ice Maker
  • Kitchen ...
  • Lobster Pot
  • Microwave ...
  • Oven
  • Pantry Items
  • Refrigerator ...
  • Stove ...
  • Stove
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 10 people
  • 4 Bathrooms
  • 1 Half Bath
  • Main Floor - toilet , HALF BATH OFF KITCHEN
    2nd South - toilet , shower enclosure , Huge bath & LARGE indoor shower with no door or curtain OPEN
    Master - toilet , shower enclosure , outdoor shower , double headed OUTDOOR shower with beautiful ocean views.
    1st South - toilet , shower enclosure , outdoor shower , double headed OUTDOOR shower with Great views! A favorite
    1st West - toilet , shower enclosure , Huge bath & indoor shower with window onto bananna trees
  • This unique bathroom flows directly from the bedroom area and allows easterly breezes to sweep through the bedroom. Double headed outdoor shower can truly double your fun. Double vanity allows each guest to have plenty of work and storage space. Plenty of light in this and all our bathrooms as we designed the lighting to be cool during the day but like a Broadway Opening at night. Most of our light fixtures are on dimmers. 'How can you get your mascara correct unless you have enough light?' Elise lamented when we rented elsewhere on Anguilla. Electricity is so expensive on the island that many location keep lighting to a minimum but not at Grand Outlook Castle. ***Photo Credit... Main sunset photo by Mr. Michel Istaphanous
  • 4 Bedrooms, Sleeps 10
  • 1st West - 1 extra lg. double bed , 1 child bed , Another Very Large ROOM 11' CEILINGS & private deck hammock!
    1st South - 1 large double bed , 1 single bed , Very Large w/11' CEILINGS & 2 sliders to pool and hammock!
    Master - 1 extra lg. double bed , 1 cot , Very Large ROOM w/ 15' CEILINGS and private deck & hammock
    2nd South - 1 large double bed , 1 single bed , Very Large ROOM 15' CEILINGS best views to the sea
  • ALL 4 Master Bedrooms with both sunrise and sunset patios. One for morning sun the other for the evening sunsets. Views from ALL bedrooms are breathtaking and you can see well about the island. Ceiling fan and fully air conditioned for your comfort as all our bedrooms are. This bedroom is actually is 78 feet in length from the end of one patio to the other; you could walk laps in this room! King size bed with chair and a chair with ottoman. A great bedroom to read and relax! Outdoor shower has two separate heads and water controls. No one gets cold and you can comfortably entertain while watching the sunset, expansive view or stars. Two large walk-in closets for plenty of storage space during your stay. Armoire has 26' Plasma TV and extensive DVD library. The TV is there but... you don't have to be exposed. Our staff can create any configuration you choose; full TV & Video, Video only OR neither at all. PLEASE CALL FOR YOUR SPECIAL DATES!!!
  • Books
  • books - fiction/non-fiction
  • books - kids
  • CD Player
  • DVD Player
  • Games
  • Radio
  • Satellite / Cable ...
  • Stereo
  • Television ...
  • Video Game Console ...
  • Video Library ...
  • Balcony ...
  • Barbecue
  • deck chairs
  • Beach Towels
  • Binoculars
  • Crow's Nest
  • Deck / Patio ...
  • Gated Community
  • Golf
  • Lanai / Gazebo ...
  • Large Cooler
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • patio
  • Veranda / Loggia
  • conservatory
  • Small Cooler
  • Terrace
  • veranda
  • Walkway to Water
  • 14 garden chairs
  • 8 beach chairs
  • Groups
  • long term rentals available
  • Low Allergen Environment
  • alternative lifestyle
  • suitable for elderly or infirm
  • wheelchair accessible ...
Pool / Spa:
  • Outdoor Pool
  • Private Pool ...
Onsite Services:
  • Car Available
  • car optional
  • Chauffeur
  • Concierge
  • Massage
  • Private Chef
  • Staff
  • bay
  • botanical garden
  • caves
  • churches
  • duty free shops
  • festivals
  • forests
  • health/beauty spa
  • marina
  • museums
  • naturist beach
  • playground
  • pond
  • recreation centre
  • reefs
  • restaurants
  • ruins
  • synagogues
Leisure Activities:
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • gambling casinos
  • horse riding
  • paddle boating
  • scenic drives
  • sight seeing
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness centre
  • groceries
  • hospital
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • golf pass optional
  • hiking
  • kayaking
  • mountain biking
  • paragliding
  • pier fishing
  • sailing
  • diving
  • snorkelling
  • snorkeling/diving
  • bay fishing
  • caving
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
Grand Outlook Castle comes with everything you will need and those items you don't are available. Children are welcome and we provide a Safety Turtle pool alarm and a secure play area just off the main deck. First floor living is easy for the elderly members. First floor bedrooms have level access to the pool, outdoor grille/dining areas, living room with three steps to the kitchen/dining areas. Communication! Very important when you are a distance from home. You have castle wide WI-FI access. Plus, The Castle comes with an international cell phone. You can receive and make calls anywhere on the island. Rates per minute to the US are very reasonable at $.336 day, $.299 evenings & $.261 on weekends. It's a pay as you go phone so you can easily manage your cost by only adding the money you want to spend. Money runs out, no calls go out but all incoming calls are Free! It's saved us hundreds of dollars!! We do ask and require ALL smoking MUST be conducted outdoors. PLEASE CALL FOR DATES!


Exceptional! 5/5 -
(127 traveller reviews)

#1 Castle Rental in Caribbean w/ 125!~ALL 5 Star Reviews!!! Come & Just RELAX!!!
average rating of 5.0 based on 135 reviews

It's all about the spice rack

  • 5 of 5

We've been fortunate to stay in many wonderful villas throughout the Caribbean, where we've been travelling for over 30 years. This was our first stay on Anguilla. It will not be our last.

The island is charming, accessible, relatively bug free, and has the most amazing beaches we've ever seen. Best part? The people are just plain wonderful. They seem to be thrilled that their little slice of heaven is enjoyed by so many folks from away, and they are all great hosts and hostesses.

Our thoughts on GOC.

1. Read the other reviews. Suspend your skeptical grumpy self, and just believe every single word. The house is as good as described, and in many ways much better. It seems to have been built as someone's home, and not just a rental place. Lots of nice detail work, interesting lighting, very upscale furnishings and great finish levels throughout. Our experience in other villas, almost uniformly, is that they are presented as nice places to stay, but rarely do we feel welcomed as we would be in our best friend's home. Paul and Elise seem to be natural hosts, and this house reflects that. EVERYTHING works and EVERYTING you need to enjoy your time away is in place. The spice rack has 25 spices, not the begrudging salt and pepper shaker we usually find. The liquor cabinet has plenty of devil rum to tide you over until a trip to the store, and the refrigerator has milk, bread, butter and eggs for your first breakfast. AND there are actually coffee filters that work with the pot!! These things don't happen by accident, and I'm trying to make the point that they are reflective of the overall experience, well thought through, generous and accommodating.

2. The pool deck is where you'll spend most of your non beach time, and it's outstanding. Again, we've learned to be picky about sun exposure, and this pool deck has sun from, literally, an hour after sunrise until sunset.

3. The view. It's the real deal. Limitless horizon to suck the stress right out of your brain for hour after hour, with lots of cool boats moored in the harbor to snoop on when you're so moved. The sunsets are right out of central casting, and demand to be toasted with an umbrella drink of some kind.

We really loved the house and location (walking distance to a couple of nice places to eat, but the walk uphill coming home is a killer), and we'll definitely return.

  • Review Submitted: Mar 3, 2015
  • Date of Stay: Feb 2015
  • Source: HomeAway
Owner's Response: Dear Anonymous, Thank You!!! Thank you for the wonderful words you have shared about the wonderful island of Anguilla and spectacular Grand Outlook Castle. We are so pleased we are the #1 villa in your 30 years of exploring the Caribbean. As you have written, Grand Outlook Castle is our "home" too and we are happy to share it with guests who want a more intimate than sterile experience; umbrella drinks of any kind included. Thank you also for the wonderful sunset video. Which we will post over on our Facebook page. It truly is an amazing representation of the castle experience. We do feel a little late in not having thought of using a time lapse video ourselves. It often amazes us with what our guests create and suggest. It really works best that way. What did you think of the hammocks... another great guest insight. We do look forward to your return and will have even more improvements and "spices" to exceed your and all our guests expectations! "it's not about the money, it's about the priceless!" Kindly, Eileen, Derrick, Elise, Charles, Mitchel, Paul, Ron and forever Mother Nature! Grand Outlook Castle Anguilla, British West Indies TGYC!
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  • 5 of 5

We dad a fantastic week at GOC.the villa and kitchen was very well equipped ,and we spent ️️lovely evenings dining at the poolside.the staff were most helpful ,making sure that we had everything that we needed to have a perfect holiday.the pool was lovely to relax in ,looking down onto the beach below .i especially loved the outdoor showers.

  • Review Submitted: Apr 19, 2017
  • Date of Stay: Mar 2017
  • Source: HomeAway
Owner's Response: Hello Jayne, Happy to have your most kind words on your group of 8's retreat to our version of True Paradise, Grand Outlook Castle. Yes, we did design the castle to accommodate multiple chefs in a large performance styled area. AND we leave many spices and some beverages behind for easy assimilation to your castle culinary fun. We have an idea why you "especially loved the outdoor showers. When we designed the outdoor showers Elise and I wanted it to be a "performance style area" like the kitchen but a tad more intimate. So, each of the castle's outdoor showers has TWO shower heads... See what I mean? As we like to say at the castle, "save time, have fun and shower together" comfortably AND isn't that what vacation is all about??? CHEERS & THANKS! Elise & Paul The Grand Outlook Castle TGYC!
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Fabulous villa! Exceeded our expectations!

  • 5 of 5

Spent a fantastic week here celebrating my husbands 60th, with 3 other couples from Scotland. From the booking, our arrival and stay, everything was well organized and straightforward. The owners sent us an information pack before we arrived, which was very helpful. GOC exceeded our expectations, providing us with spacious, luxurious accommodation, and amazing views over the ocean from the pool deck and infinity pool. The villa was extremely well equipped - all we needed were our clothes. The staff were helpful, and quick to respond to a minor issue we had. Would highly recommend this villa, and would love to be able to stay again

  • Review Submitted: Apr 18, 2017
  • Date of Stay: Mar 2017
  • Source: HomeAway
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Cincinnati, OH

Beautiful location with all amenities available in peaceful Anguilla

  • 5 of 5

We had the pleasure to stay at the Castle with three other couples for a week in March 2017. The location is unsurpassed with a fantastic view of Crocus bay and the ever-changing scene of super yachts and racing sailboats below. The property is very well maintained and has all possible amenities available for your stay. The kitchen is well stocked (pots, pans, spices, utensils, glasses, etc.) and all types of gear is available to support day trips to the local beaches (umbrellas, chairs. floats, snorkel gear, etc.) We really enjoyed the beaches at Shoal Bay (nice off shore snorkeling), Crocus bay (kayak rental at Da Vidas for trips to Little Bay and around the yachts), and Meads and Rendezvous Bay for walking and Blanchards Beach Shack. Make sure you check out Falcon's Nest a family run beach bar in Island Harbor. Grilled lobster caught by the owner (Warren) that morning - fantastic at reasonable price! Also visit Benjamin at Cafe de Paris for the best croissants and omelets on Anguilla. During our stay we encounter ed some unique issues with power, wifi, and AC in one bedroom that were quickly attended to by Gifford, the owner's island manager. Gifford was able to get a repairman out on a Sunday afternoon to fix the AC ... awesome. Thanks so much. The Gilkeys

  • Review Submitted: Mar 29, 2017
  • Date of Stay: Mar 2017
  • Source: HomeAway
Owner's Response: Dear Sam, It was a real pleasure to work with you, your bride and your very sophisticated entourage. You having both worked and travelled throughout the Caribbean for decades gives your most kind words much credibility. Elise & I truly appreciate your comment... "The location is unsurpassed with fantastic views..." We love that word "fantastic" THANK YOU! We also appreciate that you noted "all amenities available". We ourselves retreat to Grand Outlook Castle some 6 weeks a year and want it to be for our guests like returning to their own comfortable castle ... As many of our guests are repeat visitors. Our goal... is to get you relaxed the moment your enter "your castle". A few beers, a bottle of rum, a bottle of wine and many of the spices and condiments waiting for your arrival... SO you don't need a huge shopping list to get up to speed on your well deserved vacation. "HEY This is Anguilla and it is just easier here!" tm We look forward to your return and will continue to work toward making your next Grand Outlook Castle retreat an even better experience. CHEERS! Elise & Paul, Katie & Gifford, Rolyn, Sue, Junior, Ron & Wendell The Grand Outlook Castle the #1 Guest Rated Rental TGYC!
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Lincoln, MA

Our best vacation ever!

  • 5 of 5

I would like to share a few words that describe our 2 week vacation in Paradise. Peaceful, beautiful, amazing, blissful, fun, warm, quaint, casual, comfortable, outstanding sunsets, extremely safe and a ton more. This romantic home is very conveniently located at the top of the hill in highest section of Crocus. The Castel is extremely spacious, very nicely decorated, very well appointed, private and quiet. The beaches are never crowded and amazing, the food outstanding and the locals couldn't have been nicer. We cant wait to visit Anguilla island again and share our experience with the rest of our family.

Thank you Paul and Elise for allowing us to share your paradise!

Tom & Denna

  • Review Submitted: Feb 14, 2017
  • Date of Stay: Jan 2017
  • Source: HomeAway
Owner's Response: DEAR Denna & Tom... U folks are the best! So much fun helping create your experience of Grand Outlook Castle to BE... "Peaceful, beautiful, amazing, blissful, fun, warm, quaint, casual, comfortable, outstanding sunsets, extremely safe and a ton more." It was really a mutually gratifying exchange of mere money for truly priceless! THRILLED you have already booked your return; THANK YOU! Gratefully, Elise & Paul, Katie & Gifford, Sue, Rolyn, Wendell, Junior, Ron, Wilson Grand Outlook Castle Anguilla, British West Indies aka True Paradise! TGYC!
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Danvers, MA

Best vacation ever!

  • 5 of 5

This was the second year for us at Grand Outlook Castle in Anguilla. And, the eight of us are in complete agreement, it was a fabulous vacation!

Grand Outlook Castle sits atop Crocus Hill and captures an amazing view of the ocean. It is the view that grabs you the moment you walk inside the front door. At the same time you can’t help but notice how spacious the living area is on this level. The terrace with the infinity pool is an extension of the first floor. It’s the outdoor family room. In the morning, it is a great place to have a cup of coffee, read or take a swim. And in the early evening you sit by the pool with your cocktail and gaze at the sunset. It is one of the best things about the Castle.

Did I mention the kitchen? This year we prepared four gourmet dinners, Sunday brunch and several light lunches. It has everything you need! And it is well designed so that two or three can assist with meal preparation and not be in each other’s way. We were so comfortable in the Castle, we didn’t want to leave. Anguilla has some great restaurants, but our meals at the Castle were some of the best!

All bedrooms have en suite bathrooms, private balconies with hammocks and ocean views, air conditioning and very comfortable beds. Great accommodations for couples traveling together….no one gets stuck with the twin beds and the shared bath!

Grand Outlook Castle is a wonderful retreat because of its owners, Paul and Elise. They helped with the unique design of the villa, but they take care of every detail to make your stay just perfect. From the moment you contact them, their only concern is that your vacation be easy and memorable. Transportation from the airport to the Castle is arranged, rental cars are in the driveway when you arrive, the housekeeper and caretaker greet you upon arrival. Elise checks in to be sure all is well and will answer any questions you may have. They are wonderful people!

One last comment, the location of GOC on the island is also perfect. Its location in the middle of the island makes traveling to East End or West End beaches easy and quick. It is close to Sandy Ground where you find many of the restaurants and there are also numerous grocery stores nearby.

I would highly recommend Grand Outlook Castle to anyone looking to vacation on Anguilla!

  • Review Submitted: Feb 6, 2017
  • Date of Stay: Jan 2017
  • Source: HomeAway
Owner's Response: OMG Carolyn... Yours are some of the most wonderful words we have ever received. Elise and I are simply thrilled that we were able to provide you and your posse these unique experiences. PLUS... you can be certain we would be thrilled to have you back. CHEERS! Elise & Paul TGYC!
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Nearest Airport
1.6 Miles
NEW Clayton International Airport on Anguilla
Nearest Barpub
1000 Metres
DaVida on the beach just below GOC
Nearest Ferry
3.2 Miles
Blowing Point Ferry
Nearest Golf
3.5 Miles
Cuisinart Golf, Rated 3rd best in Caribbean! OPEN
Nearest Motorway
150 Miles
No such thing on Anguilla... Fortunately!
Nearest Restaurant
1000 Metres
DaVida restaurant, walking distance free loungers
Nearest Beach
1000 Metres
World Famous Little Bay a short hike or Calvin
Car: recommended

Grand Outlook Castle has been AWARDED both 'EXCELLENT RENTAL' & 'TOP ANGUILLA VACATION RENTAL' ratings for BOTH 2011, 2012 & 2013.

We are blessed and so will you!

NOW RANKED the #1 Villa Rental on Anguilla!!! At VRBO and HomeAway... Come and learn why...

We will exceed your expectations!


Thank You! prior guests for having made Grand Outlook Castle such a recognized unique accomodation.


Grand Outlook Castle has spectacular views is very safe and very secluded with easy access to THE World's Best Beaches, great restaurants & best local stores.

Nestled on the side of the 2ND highest point on Anguilla, you will be entertained by turquoise sea, beaches, sea turtles & nature. Best SUNSETS & embracing VIEWS are YOURS!


4 huge ensuite bedrooms provide privacy w/ large baths & each with big balconies. Grand Outlook Castle uniquely provides you with constant awe. Guests seldom need or want to leave. Cook in our SPACIOUS kitchen, grill by the pool or schedule our chef for a luxurious evening.


At GOC, your hardest decision IS when to break from its embrace. We arrange adventures, spa and dining so you won't have to make those decisions. Our staff is available to answer all questions whether it's your 1st or 10th stay. Guests exclaim... ''Best Vacation Ever!'' & A 'MUST return'. Our Castle is amazing! You will BE a HERO for booking Grand Outlook Castle. We NOW have 48 5-STAR REVIEWS! Most on AXA!

Other Activities: RELAX! on the World's Best Beaches from one of the World's Best Views!!! Beaches are either a walking hike away or a short ride. Driving on Anguilla is easy as the island is quite flat...

Grand Outlook Castle is within walking distance to the NEW! Pelican Trail & Water Sports at Little Bay. Serving food & drink, breakfast, lunch & dinner. Glass bottom kayak rentals, sea trampoline and guided tours of the coastline.

Also, very easy access to famous Little Bay Beach by Calvin's boat down at Crocus Bay Beach.

You can also walk to both Koal Keel and beachfront DaVida restaurants and enjoy wonderful views the entire way.

Golf: JUST 10 minutes from Grand Outlook castle, the Cusinart Golf Course has been rated the #3 course in all of the Caribbean. Greg Norman designed course with beautiful views during your entire round with many exciting and challenging holes. Five t-boxes per hole allows you to play the course at a variety of different skill levels.

EVERYONE can play on this beautiful BUT very low key golf course. There is no rushed t-times and no marshalls unless they are bringing you refreshments. It's a wonderful course to bring friends or family to play and truly enjoy a round of golf together even if their games is a challenge.

18 holes Driving Range Putting Green Carts Caddies

Par 72 slope 75.6/134

Black Tees play 7,063 yards

Gold Tees play 6,673 yards

Silver Tees play 6,243 yards

Copper Tees play 5,772 yards

Jade Tees play 5,317 yards

*** This golf course was designed so ALL levels of players can enjoy a relaxed and stress free round of golf TOGETHER in PARADISE!

Come play great golf on a great course from a great castle... Grand Outlook Castle


Rates & Availability

Rental Rates for this holiday castle in Anguilla

Rental Basis:
per property
Owner accepts payment in:
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Rate Period Nightly Weekend Night Weekly Monthly Event
2 Dec 2017 - 15 Dec 2017
5 night minimum stay
Notes: Rates are based on 5 guests; add A$67 per night, per additional guest
16 Dec 2017 - 28 Dec 2017
8 night minimum stay
Notes: Rates are based on 5 guests; add A$101 per night, per additional guest
29 Dec 2017 - 6 Jan 2018
8 night minimum stay
Notes: Rates are based on 6 guests; add A$101 per night, per additional guest
My Standard Rate
6 night minimum stay
Notes: Rates are based on 4 guests; add A$101 per night, per additional guest

Additional information about rental rates

Property Damage Protection A$79.06

Grand Outlook Castle's rates include all fees and taxes.
There are no additional charges from the rates you are quoted by the owners.
Quotes here are only estimates and require owner verification.

Services from chefs to massages or fresh fish to fresh herb are available on an ala carte basis.

Most Grand Outlook Castle base rates are for 2 bedroom use and four guests with a minor charge of

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
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